(2E,4E,6Z,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

• ChemBase ID: 159523
• Molecular Formular: C21H26O3
• Molecular Mass: 326.42934
• Monoisotopic Mass: 326.18819469
• SMILES: c1(c(cc(c(c1C)/C=C/C(=C\C=C\C(=C\C(=O)O)\C)/C)C)OC)C
• Canonical SMILES: COc1cc(C)c(c(c1C)C)/C=C/C(=C\C=C\C(=C\C(=O)O)\C)/C
• InChI: InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8-,15-12+
• InChIKey: IHUNBGSDBOWDMA-CJJRUFRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6Z,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: (2E,4E,6Z,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• Synonyms: (2E,4E,6Z,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic Acid; 9-cis Acitretin

Database IDs

• CAS Number: 419534-31-9
• PubChem SID: 162253658
• PubChem CID: 29971118

CALCULATED PROPERTIES

• Acid pKa: 5.011076
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.976502
• LogD (pH = 7.4): 3.2266924
• Log P: 5.5870485
• Molar Refractivity: 104.1665 cm^3
• Polarizability: 38.030373 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A189910

A geometrical isomer of Acitretin.

REFERENCES

• Geiger, J., et al.: Dermatologica, 176, 182 (1988)
• Blanchet-Bardon, C., et al.: J. Am. Acad. Dermatol., 24, 982 (1988)
• Suzuki, T., et al.: J. Nutr. Sci. Vitaminol., 44, 729 (1988)